Heptanoic Acid → Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide

HRID 47827

Reaction equation

HRID 47827 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]([OH:21])(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30][NH2:31])=[CH:27][CH:26]=1)([O-:24])=[O:23].C(N(CC)CC)C>C(OCC)(=O)C.C(Cl)Cl>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([CH2:29][CH2:30][NH:31][C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 8094Heptanoic AcidHCID 8471TriethylamineHCID 951534-NitrophenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86586370Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amideYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.86 g, 20.1 mmol) and heptanoic acid (2.38 mL, 16.8 mmol) were added sequentially to a solution of 4-nitrophenethylamine (3.40 g, 16.8 mmol), triethylamine (2.81 mL, 20.1 mmol) and methylene chloride (25 mL). After stirring 18 h at ambient temperature, the reaction mixture was diluted with ethyl acetate; washed sequentially with water, 1N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride; dried over anhydrous sodium sulfate; filtered and concentrated under reduced pressure to provide 3.80 g (81%) of heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide as an off-white solid.

Workup

  1. washwashed sequentially with water, 1N aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a111074eabfd4a1fb8dcd2b34b409831
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Linked notes

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